Acetic Acid → (R)-2-(Tetrahydropyranyloxy)propionic acid

HRID 1654195ノート

反応式

HRID 1654195 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH3:13])[C:9]([O:11]C)=[O:10].[OH-].[Na+].C(O)(=O)C>C(O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH3:13])[C:9]([OH:11])=[O:10]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11593565(R)-2-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

生成物 1

HCID 22852535(R)-2-(Tetrahydropyranyloxy)propionic acid収率 81%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

In ethanol (510 ml) was dissolved methyl (2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionate (42.7 g), to which was added, under ice-cooling, a 2N solution of sodium hydroxide (170 ml), followed by stirring for one hour at room temperature. The reaction mixture was cooled with ice, to which was added a 26% aqueous solution of acetic acid (120 ml), followed by extraction with dichloromethane (200 ml) three times. Dichloromethane layers were combined, washed with a saturated aqueous sodium chloride solution (100 ml) twice, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave (2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionic acid (32 g) as a colorless waxy product.

後処理

  1. additionto which was added, under ice-
  2. temperaturecooling
  3. temperatureThe reaction mixture was cooled with ice, to which
  4. extractionfollowed by extraction with dichloromethane (200 ml) three times
  5. washwashed with a saturated aqueous sodium chloride solution (100 ml) twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure

出典と根拠

ORDレコード
ord-7d18882e100a427eb117b1010d886a12
出典データセット
uspto-grants-1995_04
特許番号
US05405861

反応ノート

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